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New rearrangement in the adamantylation reaction of 4-iodophenol and 4-iodoanisole

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Abstract

A reaction of 2-iodophenol and 2-iodoanisole with 1-adamantanol in trifluoroacetic acid gives the corresponding 4-(1-adamantyl) derivatives. Similar adamantylation of 4-iodophenol and 4-iodoanisole is accompanied by migration of the iodine atom from para- to ortho-position, giving 4,6-di(1-adamantyl)-2-iodophenol and 4-(1-adamantyl)-2-iodoanisole, respectively, as the reaction products.

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Authors and Affiliations

  1. Institute of Chemistry and Chemical Technology, Siberian Branch of the Russian Academy of Sciences, 42 ul. K. Marksa, 660049, Krasnoyarsk, Russian Federation

    W. A. Sokolenko, N. M. Svirskaya & A. I. Rubailo

  2. Siberian Federal University, 79 Svobodnyi prosp., 660041, Krasnoyarsk, Russian Federation

    A. I. Rubailo

Authors
  1. W. A. Sokolenko
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  2. N. M. Svirskaya
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  3. A. I. Rubailo
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Corresponding author

Correspondence to W. A. Sokolenko.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1748–1749, August, 2011.

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Sokolenko, W.A., Svirskaya, N.M. & Rubailo, A.I. New rearrangement in the adamantylation reaction of 4-iodophenol and 4-iodoanisole. Russ Chem Bull 60, 1776–1777 (2011). https://doi.org/10.1007/s11172-011-0265-x

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  • DOI: https://doi.org/10.1007/s11172-011-0265-x

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